5-氨基-2,3-二氢-1-苯并呋喃-7-羧酸 | 920739-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 5-氨基-2,3-二氢-1-苯并呋喃-7-羧酸
• 英文名称: 5-amino-2,3-dihydrobenzo[b]furan-7-carboxylic acid
• 英文别名: 5-amino-2,3-dihydrobenzofuran-7-carboxylic acid；5-Amino-2,3-dihydro-1-benzofuran-7-carboxylic acid
• CAS: 920739-80-6
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: XVEJUCGEDMCUOH-UHFFFAOYSA-N

物化性质

• 沸点：
  433.2±45.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 正丁基锂 、 四甲基乙二胺 、 palladium 10% on activated carbon 、 氢气 、 硝酸 、 三氟乙酸 作用下， 以 乙醇 、 正己烷 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 9.5h， 生成 5-氨基-2,3-二氢-1-苯并呋喃-7-羧酸
  参考文献：
  名称：

  Discovery and Structure–Activity Relationship of Novel 2,3-Dihydrobenzofuran-7-carboxamide and 2,3-Dihydrobenzofuran-3(2H)-one-7-carboxamide Derivatives as Poly(ADP-ribose)polymerase-1 Inhibitors

  摘要：

  Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 mu M). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 mu M). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3',4'-dihydroxybenzylidene 58 (IC50 = 0.531 mu M) showing a 30-fold improvement in potency. Various heterocycles attached at the 4'-hydroxyl/4'-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 mu M). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.

  DOI：

  10.1021/jm5002502

文献信息

• Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field
  申请人：Naccari Giancarlo

  公开号：US20090118357A1

  公开（公告）日：2009-05-07

  Therefore the present invention relates specifically to the compounds of general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising H, —C n H 2n-1 , a linear or branched alkyl group having from 1 to 6 carbon atoms, or together form an aromatic or aliphatic ring with 5 or 6 atoms; R 3 is selected from —CO—CH 3 , —NHOH, —OH, —OR 6 in which R 6 is a linear or branched alkyl group having from 1 to 6 carbon atoms; R 4 is selected from H, a linear or branched alkyl group having from 1 to 6 carbon atoms, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl or allyl; R 5 , R 7 , R 8 are hydrogen atoms; or R 3 and R 4 , R 4 and R 5 , or R 7 and R 8 together form a ring, fused to the benzene, aromatic or aliphatic ring with 5 or 6 atoms comprising from 1 to 2 heteroatoms selected independently from the group comprising N, O, and use thereof in the medical field.

  因此，本发明特别涉及具有通用公式（I）的化合物，其中R1和R2，可以相同或不同，选自包括H，—CnH2n-1，具有1到6个碳原子的直链或支链烷基，或者共同形成一个含有5或6个原子的芳香族或脂肪族环；R3选自—CO—CH3，—NHOH，—OH，—OR6，其中R6是一个具有1到6个碳原子的直链或支链烷基；R4选自H，具有1到6个碳原子的直链或支链烷基，苯基，苄基，—CF3或—CF2CF3，乙烯基或烯丙基；R5，R7，R8是氢原子；或者R3和R4，R4和R5，或R7和R8共同形成一个环，与苯环，芳香族或脂肪族环融合，含有5或6个原子，并包括1到2个独立选自N，O的杂原子，及其在医疗领域的应用。
• Compounds and their Salts Specific to the PPAR Receptors and the EGF Receptors and their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20120316230A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds of formula (I), where R 1 and R 2 , which may be identical or different, are selected from the group comprising H, C n H 2n-1 , a linear or branched alkyl group having 1 to 6 carbons, or together form an aromatic or aliphatic ring with 5 or 6 atoms; R 3 is —CO—CH 3 , —NHOH, —OH, or —OR 6 where R 6 is a linear or branched alkyl group having 1 to 6 carbon atoms; R4 is H, linear or branched alkyl group having from 1 to 6 atoms, phenyl, benzyl, —CF 3 or CF 2 CF 3 , vinyl or allyl; R 5 , R 7 , R 8 are hydrogen atoms; or R 3 and R 4 , R 4 and R 5 , or R 7 and R 8 together form a ring, fused to the benzene, aromatic or aliphatic ring with 5 or 6 atoms comprising from 1 to 2 heteroatoms selected independently from the group comprising N, O, and use thereof in the medical field.

  本发明涉及式（I）的化合物，其中R1和R2，可以相同也可以不同，选择自H，CnH2n-1，具有1至6个碳的线性或支链烷基团，或者共同形成一个具有5或6个原子的芳香或脂肪环；R3为—CO—CH3，—NHOH，—OH或—OR6，其中R6为具有1至6个碳的线性或支链烷基团；R4为H，具有1至6个原子的线性或支链烷基团，苯基，苄基，—CF3或CF2CF3，乙烯基或丙烯基；R5，R7，R8为氢原子；或者R3和R4，R4和R5，或R7和R8共同形成一个环，与苯环，芳香或脂肪环共同构成一个具有1至2个杂原子的环，独立选择自N，O的群组；以及在医药领域中的应用。
• Compounds and their salts specific to the PPAR receptors and the EGF Receptors and their use in the medical field
  申请人：Naccari Giancarlo

  公开号：US08450506B2

  公开（公告）日：2013-05-28

  The present invention relates to compounds of formula (I), where R1 and R2, which may be identical or different, are selected from the group comprising H, CnH2n-1, a linear or branched alkyl group having 1 to 6 carbons, or together form an aromatic or aliphatic ring with 5 or 6 atoms; R3 is —CO—CH3, —NHOH, —OH, or —OR6 where R6 is a linear or branched alkyl group having 1 to 6 carbon atoms; R4 is H, linear or branched alkyl group having from 1 to 6 atoms, phenyl, benzyl, —CF3 or CF2CF3, vinyl or allyl; R5, R7, R8 are hydrogen atoms; or R3 and R4, R4 and R5, or R7 and R8 together form a ring, fused to the benzene, aromatic or aliphatic ring with 5 or 6 atoms comprising from 1 to 2 heteroatoms selected independently from the group comprising N, O, and use thereof in the medical field.

  本发明涉及化合物的公式（I），其中R1和R2可以相同也可以不同，选自包括H、CnH2n-1、具有1到6个碳原子的线性或支链烷基或共同形成具有5或6个原子的芳香或脂肪环；R3是-CO-CH3、-NHOH、-OH或-OR6，其中R6是具有1到6个碳原子的线性或支链烷基；R4是H、具有1到6个原子的线性或支链烷基、苯基、苄基、-CF3或CF2CF3、乙烯基或丙烯基；R5、R7、R8是氢原子；或R3和R4、R4和R5或R7和R8共同形成一个环，与苯、芳香或脂肪环共同构成具有1到2个杂原子（独立选自包括N、O的群）的环，并在医学领域中使用。
• METHODS OF TREATING HAIR RELATED CONDITIONS
  申请人：NOGRA PHARMA LIMITED

  公开号：US20150250749A1

  公开（公告）日：2015-09-10

  Provided herein are methods for enhancing epidermal regeneration in a patient in need thereof, comprising topically administering to said patient a pharmaceutically acceptable composition comprising N-acetyl-3-(4-aminophenyl)-2-methoxypropionic acid or a pharmaceutically acceptable salt or stereoisomer thereof, and a pharmaceutically acceptable excipient. For example, provided are methods for treating or ameliorating cicatricial alopecia, comprising topically administering to a patient in need thereof a pharmaceutically acceptable composition comprising the disclosed compounds. Also provided are methods for protecting hair follicle progenitor cells and compositions comprising same using the disclosed compounds.

  本文提供了一种增强病人表皮再生的方法，包括将一种药学上可接受的组合物局部施用于该病人，所述组合物包括N-乙酰基-3-(4-氨基苯基)-2-甲氧基丙酸或其药学上可接受的盐或立体异构体，以及药学上可接受的赋形剂。例如，本文提供了治疗或改善瘢痕性脱发的方法，包括将所述化合物的药学上可接受的组合物局部施用于需要治疗的病人。同时，本文还提供了使用所述化合物保护毛囊祖细胞的方法和组合物。
• METHODS OF INHIBITING HAIR GROWTH
  申请人：NOGRA PHARMA LIMITED

  公开号：US20150265514A1

  公开（公告）日：2015-09-24

  Provided herein are methods for reducing mammalian hair growth using the disclosed compounds. Also provided herein are methods of inhibiting hair growth after hair removal of an area of mammalian skin of a mammal using the disclosed compounds.

  本文提供了使用所披露的化合物减少哺乳动物毛发生长的方法。本文还提供了使用所披露的化合物抑制哺乳动物皮肤某个区域的毛发在脱毛后生长的方法。